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Is it important that the sphincters be loosened to some degree beforehand with a bigger object, say, a butt plug or a dildo? it always seems that regardless of how much I relax, i'm clenching onto the helix. Is this a relaxation problem or a 'stretching' problem?

I agree with 'waveseeker', what your are experiencing sounds like a relaxation problem. There is absolutely no necessity to force stretch your anal sphincter muscles. Trying to do so may actually injure yourself by creating small tears in the anus. It is much better for you to take the time to thoroughly relax yourself before attempting to insert your Helix. Various methods have been suggested to help accomplish this, such as taking a hot shower or bath, soaking in a hot tub/jacuzzi, having a partner (or self) perform a massage of the buttocks/anus area, a glass of wine or a beer, just listening to soothing music, whatever works for you.

I've been very fortunate and for most of the year have been able to achieve what I thought was very deep relaxation. Recently I've been attending my HMO's monthly meditation class. (based on Zazen). Now, sitting I can attain far better states of relaxation. And some of this has carried over into my sessions since I have a better relaxation standard than I did before.